Dichloromethane → HCID 86677402, compound

HRID 2089670Notes

Reaction equation

HRID 2089670 reaction equation
[NH2:1][C:2](=[N:54][C:55](=[O:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:3]1[CH:8]=[CH:7][C:6]([NH:9][C@@H:10]([C:32]2[N:36]=[C:35]([O:37][CH2:38][O:39][C:40](=[O:47])[C:41]([CH3:46])([CH3:45])[CH2:42][O:43][CH3:44])[N:34]([C:48]3[N:53]=[CH:52][CH:51]=[CH:50][N:49]=3)[N:33]=2)[C:11]2[C:12]([F:31])=[C:13]([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=2)[O:14][CH2:15][CH2:16][O:17][C:18]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[O:19])=[CH:5][CH:4]=1.[Cl:63]CCl.C(OCC)(=O)C.Cl>CC(OC)(C)C>[ClH:63].[NH2:1][C:2](=[N:54][C:55](=[O:62])[C:56]1[CH:61]=[CH:60][CH:59]=[CH:58][CH:57]=1)[C:3]1[CH:4]=[CH:5][C:6]([NH:9][C@@H:10]([C:32]2[N:36]=[C:35]([O:37][CH2:38][O:39][C:40](=[O:47])[C:41]([CH3:46])([CH3:45])[CH2:42][O:43][CH3:44])[N:34]([C:48]3[N:53]=[CH:52][CH:51]=[CH:50][N:49]=3)[N:33]=2)[C:11]2[C:12]([F:31])=[C:13]([CH:26]=[C:27]([O:29][CH3:30])[CH:28]=2)[O:14][CH2:15][CH2:16][O:17][C:18]([C:20]2[CH:21]=[CH:22][N:23]=[CH:24][CH:25]=2)=[O:19])=[CH:7][CH:8]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 21866389Hydrogen chloride-ethyl acetateHCID 54670009HCID 54670009, compound

Product 1

HCID 86677402HCID 86677402, compound

Reagents, catalysts & solvents 1

HCID 15413tert-Butyl methyl etherSolvent2×

Procedure

To a mixture of 4-pyridinecarboxylic acid 2-(3-{(R)-(4-{amino[benzoylimino]methyl}phenylamino)-[5-(3-methoxy-2,2-dimethylpropionyloxymethoxy)-1-pyrimidin-2-yl-1H-[1,2,4]triazol-3-yl]methyl}-2-fluoro-5-methoxyphenoxy)ethyl ester (Example 4d, 208 mg), dichloromethane (3 mL), and TBME (6 mL), 0.4 M hydrogen chloride-ethyl acetate solution (0.62 mL) was added dropwise at room temperature. TBME (6 mL) was added to the resulting mixture, and after stirring the resulting mixture for 10 minutes, the mixture was sonicated for 2 minutes. The precipitates were recovered by filtration, washed twice with TBME (5 mL), and dried under reduced pressure. The captioned compound (192 mg) was obtained.

Workup

  1. additionwas added dropwise at room temperature
  2. customthe mixture was sonicated for 2 minutes
  3. filtrationThe precipitates were recovered by filtration
  4. washwashed twice with TBME (5 mL)
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-12d58637b07949bf910ec195d98576e7
Source dataset
uspto-grants-2013_05
Patent number
US08436009B2

Reaction notes

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